A child riding a bicycle on a wooden boardwalk with a body of water and trees in the background.

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Winter Garden cottages

A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

1. Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is €446
includes taxes & fees
26 Oct - 27 Oct
Fire Pit & Yard: Updated Winter Garden Home!
A serene landscape with a pond, trees with Spanish moss, and a palm tree.

2. Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
10.0 out of 10, Exceptional, (1 review)
The price is €300
includes taxes & fees
19 Nov - 20 Nov
Shore Steps Cottage - Walking Distance To The Town Of Windermere
A modern kitchen with red walls, a dining area with a brown leather couch, and a bar stool.

3. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (16 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is €166
includes taxes & fees
26 Oct - 27 Oct
Downtown Cottage
A covered porch with wicker chairs and a ceiling fan.

4. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (44 reviews)
"Lovely stay in Mount Dora, perfect location, clean and quiet. Would definitely stay again."
United States
Charlotte
The price is €217
includes taxes & fees
26 Oct - 27 Oct
Historic Tremain Cottages
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

5. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is €355
includes taxes & fees
26 Oct - 27 Oct
Serenity - Family & Pet Friendly, Amazing Location
A single-story building with the number 297, a red door, and a bench outside.

6. Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Lake Mary
9.8 out of 10, Exceptional, (68 reviews)
"The Property was very clean ! Super convenient location and the perfect size for a family with 2 younger children ! Suzy was super nice !"
United States
Gary
The price is €247
includes taxes & fees
3 Nov - 4 Nov
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A hammock tied between two wooden posts, a wooden deck, and a view of a lake with trees and a clear sky.

7. Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (26 reviews)
"Very nice cottage, beautiful view"
United States
rachel c.
The price is €285
includes taxes & fees
26 Oct - 27 Oct
Cozy Lake Front Cottage
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

8. Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is €318
includes taxes & fees
5 Nov - 6 Nov
Family Resort Home w Pool, BBQ & Game Room
A yellow building with a number 8559, surrounded by greenery and a sidewalk.

9. Ei8555 - 3BR House Near Disney

Ei8555 - 3BR House Near Disney
3.0 star property
Kissimmee
The price is €291
includes taxes & fees
6 Nov - 7 Nov
Ei8555 - 3BR House Near Disney
A white building with large windows and a brick pathway leading to it.

10. The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!

The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!
College Park
10.0 out of 10, Exceptional, (55 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
The price is €294
includes taxes & fees
2 Nov - 3 Nov
The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!
A single-story mobile home with a front porch and a small deck.

11. Newly Remodeled Tiny Home 20 minutes from Disney!~

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is €194
includes taxes & fees
22 Nov - 23 Nov
Newly Remodeled Tiny Home 20 minutes from Disney!~
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

12. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is €186
includes taxes & fees
27 Oct - 28 Oct
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A small, single-story house with a gabled roof and a front porch.

13. Mount Dora Cottages

Mount Dora Cottages
3.0 star property
Mount Dora
9.4 out of 10, Exceptional, (212 reviews)
"Perfect spot"
United States
PATRICIA
The price is €211
includes taxes & fees
26 Oct - 27 Oct
Mount Dora Cottages
A well-lit garden area with a gravel pathway, decorative lights, and various plants.

14. Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Mount Dora
10.0 out of 10, Exceptional, (26 reviews)
"Great stay! Very welcoming home and very comfortable beds. Would rent again."
United States
Thomas K.
The price is €246
includes taxes & fees
30 Oct - 31 Oct
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
A patio with outdoor furniture, a wooden deck, and a basketball hoop.

15. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (22 reviews)
"We had an amazing stay! The place was beautiful, cozy, and incredibly comfortable. Even though we had to leave earlier than planned, we truly enjoyed our time here. The host was kind, responsive, and made everything easy from start to finish. We would definitely stay here again and look forward to returning in the future. Highly recommend!"
United States
Chiann M.
The price is €266
includes taxes & fees
22 Nov - 23 Nov
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A small cabin with a porch and a garage, surrounded by trees and a clear sky.

16. Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Davenport
6.8 out of 10, (3 reviews)
"Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. "
United States
Rebecca F.
The price is €143
includes taxes & fees
26 Oct - 27 Oct
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
A single-story house with a brick facade, a garage, and a well-maintained lawn.

17. Kissimmee Pool Home w/ Game Room Near Disney

Kissimmee Pool Home w/ Game Room Near Disney
3.0 star property
Indian Ridge
Kissimmee Pool Home w/ Game Room Near Disney
An aerial view of a resort with multiple swimming pools, palm trees, and a golf course.

18. Upstay Disney 5BR Movie Mansionwindsor Cay Resort

Upstay Disney 5BR Movie Mansionwindsor Cay Resort
3.0 star property
Clermont
The price is €403
includes taxes & fees
28 Oct - 29 Oct
Upstay Disney 5BR Movie Mansionwindsor Cay Resort
A modern multi-story residential building with a flat roof, large windows, and a well-maintained front yard with a palm tree and shrubs.

19. Mvy7632 - 4BR House Near Disney

Mvy7632 - 4BR House Near Disney
3.0 star property
Kissimmee
The price is €425
includes taxes & fees
3 Nov - 4 Nov
Mvy7632 - 4BR House Near Disney
An aerial view of a resort with multiple swimming pools, a dock, and a residential area with houses.

20. Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
Kissimmee
The price is €738
includes taxes & fees
2 Nov - 3 Nov
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Garden Hotel Reviews

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

10/10 Excellent
"Location is perfect for Disney access for work or pleasure."
Kai 11-night trip
Posted 1 hour ago
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
447
Accommodation
2643 Cottages
Lowest Price
€143
Highest Price
€738

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between €143 and €738 per night. These stays offer a chance to get reacquainted with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Winter Garden with Expedia?
Expedia has some great cottages in Winter Garden, so get ready for a memorable holiday on nature's doorstep. If you're sticking to a budget, select how much you'd like to spend and the preferred star rating of your property. Or, use our filters to search for cottages with free WiFi or a kitchen. We'll help you find the right fit whatever your bank balance or plans.
How can I find cheap cottages in Winter Garden?
With Expedia's convenient filter tool, scoring cheap cottages in Winter Garden has never been simpler. To discover accommodation that'll make your wallet happy, fine-tune your search results by budget, star rating and amenities.
What is there to do in Winter Garden near my cottage?
Whatever you're into, Winter Garden has plenty of things to keep you on the go. Orange County National Golf Club, Resurrection Catholic Church and West Orange Trail are on many travellers' agendas. Don't forget to explore Winter Garden Art Association, Winter Garden Heritage Museum and Oakland Nature Preserve either. With Expedia's Winter Garden hotel deals, you'll be able to see more renowned attractions like these with the cash you save.